Acetic Anhydride → HCID 11299280, compound

HRID 1011882Notes

Reaction equation

HRID 1011882 reaction equation
[N:1]([C@@H:4]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][C@H:5]1[OH:16])=[N+]=[N-].[H][H].[C:19](OC(=O)C)(=[O:21])[CH3:20]>CO.[Ni]>[CH2:9]([N:7]1[CH2:6][C@@H:5]([OH:16])[C@H:4]([NH:1][C:19](=[O:21])[CH3:20])[CH2:8]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 14612533HCID 14612533, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11299280HCID 11299280, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of (trans)-4-azido-1-benzyl-pyrrolidin-3-ol (0.6 g, 3 mmol) (prepared as described in J. Med. Chem 1990, 33, 5, 1344) in MeOH (10 ml) was added Rainey nickel (0.5 g) and the reaction was stirred under one atmosphere of hydrogen for 1 h. The reaction was then filtered through Hyflo and concentrated. The residue was redissolved in CH2Cl2 (5 ml) and added to saturated NaHCO3 (5 ml) and stirred vigorously while acetic anhydride (0.2 ml, 2 mmol) was added. The reaction was stirred for 15 minutes after which time the organic was separated, were dried (Na2SO4) and concentrated. Purification by flash column chromatography (CH2Cl2:MeOH 9:1) afforded the title product (0.4 g, 68%). MS: 235.1 (MH+).

Workup

  1. filtrationThe reaction was then filtered through Hyflo
  2. concentrationconcentrated
  3. dissolutionThe residue was redissolved in CH2Cl2 (5 ml)
  4. additionadded to saturated NaHCO3 (5 ml)
  5. additionwas added
  6. customorganic was separated
  7. dry with materialwere dried (Na2SO4)
  8. concentrationconcentrated
  9. customPurification by flash column chromatography (CH2Cl2:MeOH 9:1)

Sources & evidence

ORD record
ord-3ad1f2e41675427991a6e49680bb4a0e
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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